Ammonia → HCID 13869780, compound

Participants

Reaction Steps

A mixture of 2-amino-6-azido-9-[2-(2,2-dimethyl-1,3-dioxan-5-yl)ethyl]purine (318 mg, 1.0 mmol), formic acid (0.15 ml, 4.0 mmol), concentrated ammonia (0.22 ml, 4.0 mmol), 10% palladium-on-charcoal (30 mg) and methanol (10 ml) was heated under reflux for 1 hour. The solution was allowed to cool, filtered and the solvent removed. The residue was purified by column chromatography on silica gel eluting with chloroform-methanol mixtures (20:1 and 15:1) to give 2,6-diamino-9-[2-(2,2-dimethyl-1,3-dioxan-5-yl)ethyl]purine (190 mg, 65%), m.p. 202°-204° C.); νmax (KBr) 1670, 1640, 1595, and 1410 cm-1 ; δH (CDCl3 -CD3OD) 1.42 (6 H, s, C(CH3)2), 1.6-2.0 (3 H, m, CHCH2CH2), 3.5-4.2 (6 H, m, 2×CH2O and CH2N), and 7.68 (1 H, s, 8-H) (Found: C, 52.88; H, 6.78; N, 28.36%; M+ 292.1652, C13H20N6O2 requires C, 53.41; H, 6.90; N, 28.75%; M+ 292.1648).

Provenance & Evidence